Lithium borohydride → Benzyl 2-(Hydroxymethyl)-1-Indolinecarboxylate

HRID 1245028ノート

反応式

HRID 1245028 の反応式
[BH4-].[Li+].[CH2:3]([O:10][C:11]([N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH:14]1[C:22](OC)=[O:23])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O1CCCC1>[CH2:3]([O:10][C:11]([N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH:14]1[CH2:22][OH:23])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

参加物

4

反応物 2

HCID 4148881Lithium borohydrideHCID 12153759Methyl 1-benzyloxycarbonylindoline-2-carboxylate

生成物 1

HCID 2776402Benzyl 2-(Hydroxymethyl)-1-Indolinecarboxylate収率 83.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

4.6 g (212 mmol) of lithium borohydride were added in three portions to a solution of 33.0 g (106 mmol) of methyl 1-benzyloxycarbonylindoline-2-carboxylate in 450 ml of tetrahydrofuran, and the resulting mixture was stirred for 5 hours at room temperature. At the end of this time, ice was added and the mixture was stirred for a further 1 hour before extracting with ethyl acetate. The organic extract was washed with water, dried over anhydrous magnesium sulfate and then concentrated by evaporation under reduced pressure. The resulting residue was purified by chromatography on a silica gel column using a 2:5 by volume mixture of ethyl acetate and hexane as the eluant to afford 25.0 g (yield: 83%) of the title compound as a colorless oil.

後処理

  1. additionAt the end of this time, ice was added
  2. stirringthe mixture was stirred for a further 1 hour
  3. extractionbefore extracting with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated by evaporation under reduced pressure
  8. customThe resulting residue was purified by chromatography on a silica gel column
  9. additionby volume mixture of ethyl acetate and hexane as the eluant

出典と根拠

ORDレコード
ord-f5988236636a465e8769139dadbe0e77
出典データセット
uspto-grants-2006_10
特許番号
US07122666B2

反応ノート

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